Here's two cents for ya,
I have been running the same boat for 7 years, I have slowly dumped money into it over the 7 years I paid a reasonable amount and am sure I can at least get my money out that I paid for the purchase.
like it was said above if you are gonna buy used, you better get a good hull.
I went with a late 70's Hallett. Great timeless boat. It eats gas, but I have run it from below parker to as far up as mead. paid cash so when it sits big deal.
I'm now looking to up grade to a bigger boat so I am doing research as we speak. Looking to pay cash again, and buy something I can get out of if I need to. I am in the const. biz as well so I am always looking for the down turn. I found that if I'm not dumping coin on interest I like my boat alot better. Nothing worse then a payment on something you don't have time to use.
For what its worth.... good luck.